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(S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester, also known as Sarafotoxins S6C, is a chemical compound that serves as a specific antagonist for endothelin receptors. It is characterized by its potent vasoconstrictor properties and has demonstrated potential in the treatment of various cardiovascular diseases. Furthermore, its neuroprotective properties have garnered interest in the field of neuroscience. The isopropyl ester form of this compound enhances its lipophilicity, which allows for improved penetrability in lipid-rich tissues, making it a promising candidate for medical and research applications, particularly in cardiovascular and neurological health.

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  • (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylaMino]propionic acid Isopropyl ester

    Cas No: 1256490-49-9

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  • (S)-2-[(R)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

    Cas No: 1256490-49-9

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  • 1256490-49-9 Structure
  • Basic information

    1. Product Name: (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester
    2. Synonyms: N-[(R)-(4-Nitrophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester;L-Alanine, N-[(R)-(4-nitrophenoxy)phenoxyphosphinyl]-, 1-methylethyl ester;(S)-2-[(R)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester;(S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylaMino]propionic acid Isopropyl ester
    3. CAS NO:1256490-49-9
    4. Molecular Formula: C18H21N2O7P
    5. Molecular Weight: 408.3477
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1256490-49-9.mol
  • Chemical Properties

    1. Melting Point: 42-43℃
    2. Boiling Point: 514.3±60.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: 1.302±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: -5.78±0.70(Predicted)
    10. CAS DataBase Reference: (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester(CAS DataBase Reference)
    11. NIST Chemistry Reference: (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester(1256490-49-9)
    12. EPA Substance Registry System: (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester(1256490-49-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1256490-49-9(Hazardous Substances Data)

1256490-49-9 Usage

Uses

Used in Biochemical Research:
(S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester is used as a specific antagonist for endothelin receptors in biochemical research for studying the role and function of these receptors in various physiological processes.
Used in Cardiovascular Applications:
In the pharmaceutical industry, (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester is used as a potent vasoconstrictor agent for the treatment of various cardiovascular diseases, such as hypertension and heart failure.
Used in Neuroprotective Applications:
(S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester is used as a neuroprotective agent in the field of neuroscience for its potential to protect neurons from damage and degeneration, which could be beneficial in the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's disease.
Used in Drug Delivery Systems:
In the field of drug delivery, (S)-2-[(S)-(4-Nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid Isopropyl ester is used to enhance the lipophilicity of drugs, allowing for improved penetrability in lipid-rich tissues and potentially increasing the bioavailability and therapeutic outcomes of certain medications.

Check Digit Verification of cas no

The CAS Registry Mumber 1256490-49-9 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,5,6,4,9 and 0 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1256490-49:
(9*1)+(8*2)+(7*5)+(6*6)+(5*4)+(4*9)+(3*0)+(2*4)+(1*9)=169
169 % 10 = 9
So 1256490-49-9 is a valid CAS Registry Number.

1256490-49-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-2-[(R)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1256490-49-9 SDS

1256490-49-9Relevant articles and documents

Enzyme-Catalyzed Kinetic Resolution of Chiral Precursors to Antiviral Prodrugs

Xiang, Dao Feng,Bigley, Andrew N.,Desormeaux, Emily,Narindoshvili, Tamari,Raushel, Frank M.

, p. 3204 - 3211 (2019/08/20)

Nucleoside analogues are among the most common medications given for the treatment of viral infections and cancers. The therapeutic effectiveness of nucleoside analogues can be dramatically improved by phosphorylation. The ProTide approach was developed u

PROCESS FOR THE PREPARATION OF (Sp)-SOFOSBUVIR AND INTERMEDIATES THEREOF

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Page/Page column 11, (2018/03/28)

The present invention is directed towards process for preparation of an optically pure (Sp)-Sofosbuvir of Formula-(I) and its intermediate namely (Sp)-isomer of isopropyl alanyl phosphoramidate of Formula (III) thereof.

DIOXOLANE ANALOGUES OF URIDINE FOR THE TREATMENT OF CANCER

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Page/Page column 52; 53, (2016/03/22)

The invention provides compounds of formula (I), wherein: R1 is OR11, or NR5R5'; R2 is H or F; R5 is H, C1-C6alkyl, OH, C(=O)R6, O(C=O)R6 or O(C=O)OR6; R5′ is H or C1-C6alkyl; R6 is C1-C6alkyl or C3-C7cycloalkyl; R13 is H, phenyl, pyridyl, benzyl, indolyl or naphthyl wherein the phenyl, pyridyl, benzyl, indolyl and naphthyl is optionally substituted with 1, 2 or 3 R22; and the other variables are as defined in the claims, which are of use in the treatment of cancer, and related aspects.

Discovery of the first C -nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients

Cho, Aesop,Zhang, Lijun,Xu, Jie,Lee, Rick,Butler, Thomas,Metobo, Sammy,Aktoudianakis, Vangelis,Lew, Willard,Ye, Hong,Clarke, Michael,Doerffler, Edward,Byun, Daniel,Wang, Ting,Babusis, Darius,Carey, Anne C.,German, Polina,Sauer, Dorothea,Zhong, Weidong,Rossi, Stephen,Fenaux, Martijn,McHutchison, John G.,Perry, Jason,Feng, Joy,Ray, Adrian S.,Kim, Choung U.

, p. 1812 - 1825 (2014/04/03)

Hepatitis C virus (HCV) infection presents an unmet medical need requiring more effective treatment options. Nucleoside inhibitors (NI) of HCV polymerase (NS5B) have demonstrated pan-genotypic activity and durable antiviral response in the clinic, and they are likely to become a key component of future treatment regimens. NI candidates that have entered clinical development thus far have all been N-nucleoside derivatives. Herein, we report the discovery of a C-nucleoside class of NS5B inhibitors. Exploration of adenosine analogs in this class identified 1′-cyano-2′-C-methyl 4-aza-7,9-dideaza adenosine as a potent and selective inhibitor of NS5B. A monophosphate prodrug approach afforded a series of compounds showing submicromolar activity in HCV replicon assays. Further pharmacokinetic optimization for sufficient oral absorption and liver triphosphate loading led to identification of a clinical development candidate GS-6620. In a phase I clinical study, the potential for potent activity was demonstrated but with high intra- and interpatient pharmacokinetic and pharmacodynamic variability.

METHODS FOR THE PREPARATION OF DIASTEROMERICALLY PURE PHOSPHORAMIDATE PRODRUGS

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, (2012/02/05)

Provided are methods and intermediates for preparing diastereomerically pure phosphoramidate prodrugs of nucleosides of Formulas (la) and (lb): The compounds of Formula la and lb are useful for the treatment Hepatitis C infections.

1'-SUBSTITUTED PYRIMIDINE N-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT

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Page/Page column 70, (2012/10/23)

Provided are compounds of Formula I: nucleosides, nucleoside phosphates and prodrugs thereof, wherein R6 is CN, ethenyl, 2-haloethen-1-yl, or (C2-C8)-alkyn-1-yl. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections.

Synthesis of diastereomerically pure nucleotide phosphoramidates

Ross, Bruce S.,Ganapati Reddy,Zhang, Hai-Ren,Rachakonda, Suguna,Sofia, Michael J.

, p. 8311 - 8319 (2012/01/03)

Prodrugs of therapeutic nucleoside monophosphates masked as phosphoramidate derivatives have become an increasingly important class of antiviral drugs in pharmaceutical research for delivering nucleotides in vitro and in vivo. Conventionally, phosphoramidate derivatives are prepared as a mixture of two diastereomers. We report a class of stable phosphoramidating reagents containing an amino acid ester and two phenolic groups, one unsubstituted and the other with electron-withdrawing substituents. The reagents can be isolated as single diastereomers and reacted with the 5′-hydroxyl group of nucleosides through selective nucleophilic displacement of the substituted phenol to prepare single diastereomer phosphoramidate products. This method has been used to prepare the HCV clinical candidate PSI-7977 in high yield and high diastereomeric purity.

N- [ (2 ' R) -2 ' -DEOXY-2 ' -FLUORO-2 ' -METHYL-P-PHENYL-5 ' -URIDYLYL] -L-ALANINE 1-METHYLETHYL ESTER AND PROCESS FOR ITS PRODUCTION

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Page/Page column 50, (2010/12/18)

Disclosed herein are nucleoside phosphoramidates of formula 4 and their use as agents for treating viral diseases. These compounds are inhibitors of RNA-dependent 5 RNA viral replication and are useful as inhibitors of HCV NS5B polymerase, as inhibitors of HCV replication and for treatment of hepatitis C infection in mammals. Disclosed is also a process for preparing compound represented by formula 4: (Formula 4) wherein P* represents a chiral phosphorus atom, which comprises: a) reacting an isopropyl-alanate, (Formula A), a di-X'-phenylphosphate, (Formula B), 2'-deoxy-2f-fluoro-2'-C-methyluridine, (Formula 3), and a base to obtain a first mixture comprising 4; wherein X is a conjugate base of an acid, n is 0 or 1, and X' is a halogen, b) reacting the first mixture with a protecting compound to obtain a second mixture comprising 4; and c) optionally subjecting the second mixture to crystallization, chromatography or extraction in order to obtain 4.

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